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将 Barbier 反应引入到聚合化学中。

The introduction of the Barbier reaction into polymer chemistry.

机构信息

State Key Laboratory of Heavy Oil Processing, Centre for Bioengineering and Biotechnology, and College of Science, China University of Petroleum (East China), 66 Changjiang West Road, Qingdao Economic Development Zone, Qingdao, Shandong, 266580, People's Republic of China.

出版信息

Nat Commun. 2017 Oct 31;8(1):1210. doi: 10.1038/s41467-017-01472-w.

DOI:10.1038/s41467-017-01472-w
PMID:29084940
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC5662735/
Abstract

The Barbier reaction, a widely utilized reaction for carbon-carbon bond formation, has played important roles in modern organic chemistry for more than a century. Here, we show its successful introduction to polymer chemistry. Through one-pot Barbier polyaddition (both A+B type and AB type) of monomers containing an organic halide and a benzoyl group, a series of phenylmethanol group containing polymers, including polymonophenylmethanol (PMPM), polydiphenylmethanol (PDPM), and polytriphenylmethanol (PTPM), have been synthesized. Para-PTPM exhibits interesting aggregation-induced emission, tunable thermo-responsive over a wide temperature range, sensory, luminescence enhancement of fluorescent dye in solid-state and processing properties. This significantly expands the libraries of monomer and polymer, and opens up an avenue for the design and application of functional polymer materials.

摘要

巴尔比耶反应是一种广泛应用于碳-碳键形成的反应,在现代有机化学中已有一个多世纪的重要作用。在这里,我们成功地将其引入到聚合物化学中。通过含有有机卤化物和苯甲酰基的单体的一锅法巴尔比耶加成(A+B 型和 AB 型),我们合成了一系列含有苯甲醇基团的聚合物,包括单苯甲醇均聚物(PMPM)、二苯甲醇均聚物(PDPM)和三苯甲醇均聚物(PTPM)。对-三苯甲醇均聚物表现出有趣的聚集诱导发射,在很宽的温度范围内可调温响应,具有传感性,固态下荧光染料的发光增强和加工性能。这显著扩展了单体和聚合物的库,并为功能聚合物材料的设计和应用开辟了道路。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/79e8/5662735/a7c3f44aa88c/41467_2017_1472_Fig5_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/79e8/5662735/d7f8ce223ba4/41467_2017_1472_Fig1_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/79e8/5662735/d5c905779243/41467_2017_1472_Fig2_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/79e8/5662735/83237f522b46/41467_2017_1472_Fig3_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/79e8/5662735/2fa00ea09abc/41467_2017_1472_Fig4_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/79e8/5662735/a7c3f44aa88c/41467_2017_1472_Fig5_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/79e8/5662735/d7f8ce223ba4/41467_2017_1472_Fig1_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/79e8/5662735/d5c905779243/41467_2017_1472_Fig2_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/79e8/5662735/83237f522b46/41467_2017_1472_Fig3_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/79e8/5662735/2fa00ea09abc/41467_2017_1472_Fig4_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/79e8/5662735/a7c3f44aa88c/41467_2017_1472_Fig5_HTML.jpg

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Barbier Self-Condensing Ketyl Polymerization-Induced Emission: A Polarity Reversal Approach to Reversed Polymerizability.巴比耶自缩合酮基聚合诱导发光:一种实现反向聚合性的极性反转方法。
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